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Polyvinyl ethers having silicon-containing functional groups or atomic groups at the end and process for production thereof

a technology of polyvinyl ethers and functional groups, applied in the field of polymer materials, can solve the problems of inconvenient use of chlorosilane, no concrete means are available for obtaining such a polyvinyl ester,

Inactive Publication Date: 2006-06-29
JAPAN SCI & TECH CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0008] The present inventors have made continued studies and accomplished the present invention based on a surprising finding that the polynuclear ruthenium-carbonyl complex when used in combination with a specific silane compound serves as a highly-active catalyst for the polymerization of a general type of (i.e. non-cyclic) vinyl ether as well as that of the cyclic vinyl ether, thereby enabling the production of the above-mentioned objective polyvinyl ether.

Problems solved by technology

However, no concrete means are available for obtaining such a polyvinyl ester.
Furthermore, use of the chlorosilane encounters a handling problem because chlorosilane easily decomposes due to hydrolysis, thereby producing hydrochloric acid.

Method used

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  • Polyvinyl ethers having silicon-containing functional groups or atomic groups at the end and process for production thereof
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  • Polyvinyl ethers having silicon-containing functional groups or atomic groups at the end and process for production thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

Syntheses of Polyvinyl Butyl Ether and Other Materials

[0033] Into a 30 ml round-bottom flask with two necks equipped with a three-way cock, in which the air had been replaced with nitrogen gas, there were added 2.15 mg (3.3×10−3 mmol) of acenaphthylene heptacarbonyl ruthenium (the polynuclear ruthenium-carbonyl complex as expressed by the formula (V): hereinafter sometimes referred to simply as the “Ru complex”) as the catalyst, 0.05 ml of 1,4-dioxane as the solvent, and 0.050 ml (0.33 mmol) of dimethylphenylsilane (HSiMe2Ph) as the silane compound. After stirring at room temperature (25° C.) for thirty minutes, there was added 0.43 ml (3.3 mmol) of tert-butyl vinyl ether (tBuVE) as the vinyl ether compound. The resultant solution was stirred at room temperature for ten minutes, and then the 1,4-dioxane and the excess phenyldimethyl silane were distilled off. Into the residual viscous liquid was dissolved in 2 ml of hexane. Following the addition of methanol 6 ml, the resultant whi...

example 2

Comparison with Other Types of Catalysts

[0041] The polynuclear ruthenium-carbonyl complex catalyst according to the present invention was compared with the conventionally proposed cobalt complex catalyst and the platinum complex catalyst with respect to catalyst performance for the polymerization reaction of the vinyl ether. The polynuclear ruthenium-carbonyl complex catalyst was the same Ru catalyst as used in Example 1, while the cobalt complex catalyst was Co2(CO)8 and the platinum complex catalyst was H2PtCl6.6H2O. The procedure of the reactions and the analysis of products were made in the same manner as in Example 1. The polymerization reactions were carried out at room temperature with tBuVE as the monomer (the starting vinyl ether) and HSiMe2Ph as the silane compound in which the ratio of the monomer to the silane was 10:1. The results are summarized in Table 2.

TABLE 2ReactionCatalystTimeConversionYieldComplex(mol %)(hr)(%)(%)MnMw / MnRu Complex*0.10.02958590001.2Ru Complex...

example 3

Studies on Reaction Conditions

[0043] The polymerization reactions of iBuVE (isobutyl vinyl ether) were carried out using the Ru catalyst in the presence of HSiMe2Ph as the silane compound in the same manner as in Example 1, at varying monomer (the vinyl ether compound) / silane (the silane compound) ratio and reaction temperature. The results are summarized in Table 3.

TABLE 3CatalystReactionReactionRunMonomer / ConcentrationTemperatureTimeConversionNo.Silane(mol %)(° C.)(min.)MnMw / Mn(%)Yield1 1:0.010.123180290006.5243621:0.10.12360100002.7959831:1  0.1236020002.1916141:0.10.1604065003.4998251:0.10.1804048003.49890

[0044] As can be seen from Table 3, it is possible to control the molecular weight and molecular weight distribution of the product polymer by varying the monomer / silane ratio and the reaction temperature. For example, there can be obtained a polymer which has a relatively small molecular weight but has a narrower molecular weight distribution (lower Mw / Mn), by increasing th...

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Abstract

Disclosed is a technology for the production of polyvinyl ethers having a reactive silicon-containing functional or atomic group at the terminal thereof. The polyvinyl ether as expressed by the formula (VII) is prepared by allowing, in the presence of a catalyst composed of a polynuclear ruthenium-carbonyl complex in which carbonyl groups coordinate with two to four ruthenium atoms, a vinylether compound expressed by the formula (III) to react with a silane compound expressed by the formula (IV). In the formulae, R1, R2 and R3 each represents a hydrogen atom or a hydrocarbon group having 1 to 8 carbon atoms, R4 represents an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, or a silyl group, and X1, X2 and X3 each represents a hydrogen atom, a halogen atom, an amino group, an alkyl group, an alkoxy group, a thioalkyl group, an alkylamino group, an aryl group, an arylamino group, an aralkyl group a vinyl group, or a heterocyclic group.

Description

TECHNICAL FIELD [0001] The present invention belongs to the technical field of polymeric materials, and particularly relates to polyvinyl ethers having a silicon-containing functional or atomic group at the terminal thereof and a method for producing the same. BACKGROUND ART [0002] Polyvinyl ethers are industrially important materials as they are used as materials for electronic parts, lubricants, adhesives and so on. Realization of the ability to provide a polyvinyl ether with a reactive silicon-containing functional group, such as silyl group or siloxy group, at the terminal thereof, can be expected to lead to the creation of a variety of novel functional materials, by combining another compound (molecule) with the polyvinyl ether via such functional group or by replacing the functional group with another functional group. However, no concrete means are available for obtaining such a polyvinyl ester. More specifically, although there have hitherto proposed polymerization reactions...

Claims

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Application Information

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IPC IPC(8): C08F4/46C08F4/26C08F4/80C08F16/14
CPCC08F16/14
Inventor NAGASHIMA, HIDEOMATSUBARA, KOUKI
Owner JAPAN SCI & TECH CORP